Don't have a specific topic or start here, but loads of thoughts on the subject seeing as I can relate to this idea on many levels. So many, that this may well turn out as just another surface level comment. The idea of the web being a surrogate source of information without emotional connection has been a consistent theme/thought from my time on it - ya know, most of my life so far as I can recall.

Over time, mostly through gaming communities (Shadowgun: Deadzone, Minecraft, sub-communities I've kept in touch with today from years ago), I've stumbled into and grew up with different circles of online friends. It's allowed for an easier pick-and-choose of relationships as I could just "drop" a ball I'm juggling or come back to it just as easily with the excuse of "life getting in the way". On the other hand, they were easier maintain seeing as the online forms tended to have an international crowd allowing for interactions at anytime - none of these having social consequences with my own life, I could simply switch them off and continue life as it was "IRL". Though as I've grown used to this mode of communication more and more, I've developed a better insight into navigating online groups, I've grown to severely lack them in person (feeding into my own thoughts of self-worth, and that just becomes its own vicious cycle for some other discussion). But one odd complexity I've found in the communities I've kept in touch with for so long is connection.

Years on the internet in terms of gaming is a long time, I think we all can agree. This length of time tends to take relationships out of a game and into daily lives, in my experience. That is to say, people go into a game, find people they enjoy interacting/playing with, and establish forms of communication outside of it. These forms, in my experience, include various forums, google hangouts, Skype, Facebook (using their personal accounts, mind you), online messengers, and newer mediums such as Discord and the like. Using these extensions of the internet I've grown to, genuinely, care about lives of peoples around the world - as I've seen expressed in so many words here of other users. Interestingly, the extent others have been willing to divulge, or rather seek out help other than their parents, per se (keeping somewhat in-line with your post) varies vastly by culture. People will talk about day-to-day life, yes. In some places, conversations can become heavy with emotional weight attached.

My own experience of these two sorts of bonds I've invested years into compared to my "real life," again find me severely lacking in social skills short circuiting my ability to make meaningful connections as quick as I would like to. As a result, the path of least resistance is to default back to online - frankly, my aversion to 'real interactions' as a result becoming habitual I think may contribute to the diagnosis of Aspergers, but that's blind speculation unsubstansiated, neither here nor there. Back on topic, the catch despite inordinate amount of time spent fleshing out one's soul online doesn't produce that same result if repeated face-to-face.

After juxtaposing the time spent and conversations on online communities versus entrenched volunteering in those 'therapy retreats' as I'd like to call them, there's nothing that can convince me otherwise. A key element in the dichotomy I'd like to attribute to the gap in efficacy is in part as bl00's stated is tailored context paired with the development (or mere channeling) of what empathy would look like. With regard to context, it can be gained in years of sustained, open connection online, but even through video, there's nothing I've experienced like seeing someone's empathy or compassion in chorus with body language to tell you that you've been heard.